Potassium Hydroxide → HCID 67166457, compound

HRID 552378Notes

Reaction equation

HRID 552378 reaction equation
[CH2:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[C:5]=1[C:6]([O:8]C)=[O:7])[CH:2]=[CH2:3].[OH-].[K+]>C(O)C>[CH2:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[C:5]=1[C:6]([OH:8])=[O:7])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67166341HCID 67166341, compound

Product 1

HCID 67166457HCID 67166457, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Step 2 intermediate (3.0 g, 15.7 mmol) in ethanol (10 ml) was added 2.0 M potassium hydroxide (4.0 ml) and the mixture was refluxed for 3 h. The mixture was concentrated under reduced pressure and diluted with water. The basic aqueous solution containing the product was washed with diethyl ether (2×25 ml). The aqueous solution was acidified to pH 4.0 with 1N HCl. The solid separated out was filtered and washed with water and dried to give 550 mg of the product as an off-white solid; 1H NMR (δ ppm, CDCl3, 300 MHz): 7.01 (t, J=9.0, 1H); 6.57 (d, J=9.0, 1H); 6.36 (d, J=9.0, 1H); 5.94-5.79 (m, 1H); 5.02-4.90 (m, 2H); 3.46 (d, J=6.0, 2H).

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additiondiluted with water
  4. additionThe basic aqueous solution containing the product
  5. washwas washed with diethyl ether (2×25 ml)
  6. customThe solid separated out
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-011adf86833f48258e5f6aa0bc4bfe44
Source dataset
uspto-grants-2011_05
Patent number
US07951814B2

Reaction notes

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